Potassium Carbonate → 4-(3-Butyl-1,4-dihydro-4-oxo-quinolinyl methyl)-benzonitrile

HRID 1602933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1602933
[C:1](=O)([O-])[O-].[K+].[K+].[CH2:7]([C:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10].Br[C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1>CC(C)=O>[CH2:7]([C:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:1][C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[CH:12]=1)[CH2:8][CH2:9][CH3:10]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 12162Benzonitrile, 4-bromo-HCID 195953413-butyl-4-(1H)-quinolinone

Produkt 1

HCID 196085034-(3-Butyl-1,4-dihydro-4-oxo-quinolinyl methyl)-benzonitrileAusbeute 113,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

3.3 g of activated potassium carbonate were added to a suspension of 2.3 g of the product of Step E in 50 ml of acetone a the mixture was stirred for 10 minutes. Then, 4.7 g of 4-bromobenzonitrile were added, followed by heating for 4 hours at reflux. The acetone was evaporated off and the residue was taken up in 100 ml of water. Extraction was carried out with ethyl acetate and the extracts were washed with a saturated solution of ammonium chloride, dried and evaporated to dryness to obtain 4.1 g of the expected product which was chromatographed on silica (eluant: methylene chloride-methanol (98-2)) to obtain 3.3 g of the desired product melting at 168° C.

Aufarbeitung

  1. temperatureby heating for 4 hours
  2. temperatureat reflux
  3. customThe acetone was evaporated off
  4. extractionExtraction
  5. washthe extracts were washed with a saturated solution of ammonium chloride
  6. customdried
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ed6aad7ef91740ed8914cefcfa7eeb73
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05985894

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